methyl cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanecarboxylate | 85121-45-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanecarboxylate
• 英文别名: methyl (1R,3S)-3-hydroxy-2,2-dimethyl-6-methylidenecyclohexane-1-carboxylate
• CAS: 85121-45-5
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: MWLLUJQOCRDLCR-IUCAKERBSA-N

物化性质

• 沸点：
  262.7±40.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanecarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到(1RS,3SR)-3-(hydroxymethyl)-2,2-dimethyl-4-methylenecyclohexanol
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

  摘要：

  A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00335-x
• 作为产物：
  描述：

  methyl Z-3-(diethylphosphoryloxy)-7-methyl-2,6-octadienoate 在 potassium osmate(VI) 、 甲基磺酰胺 bis(acetylacetonate)nickel(II) 、 (DHQD)2PHAL 、 三氟化硼乙醚 、 potassium carbonate 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 33.0h， 生成 methyl cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanecarboxylate
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

  摘要：

  A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00335-x

文献信息

• Armstrong, Rosemary J.; Weiler, Larry, Canadian Journal of Chemistry, 1986, vol. 64, p. 584 - 596
  作者：Armstrong, Rosemary J.、Weiler, Larry

  DOI：——

  日期：——
• Armstrong, Rosemary J.; Weiler, Larry, Canadian Journal of Chemistry, 1983, vol. 61, p. 214 - 216
  作者：Armstrong, Rosemary J.、Weiler, Larry

  DOI：——

  日期：——
• Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone
  作者：Simon D. Schnell、Anthony Linden、Karl Gademann

  DOI：10.1021/acs.orglett.9b00090

  日期：2019.2.15

  A concise route toward two advanced fragments in the context of the total synthesis of the unique natural product azamerone is reported. Key synthetic features include the enantioselective synthesis of an epoxysilane and its Lewis-acid-induced cyclization and the installation of the pyridazine ring via a formylation/condensation sequence. This route provides strategic insights into the chemistry of phthalazinediols, facilitating synthetic approaches toward this class of natural products.
• Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether
  作者：Stephen Beszant、Elios Giannini、Giuseppe Zanoni、Giovanni Vidari

  DOI：10.1016/s0957-4166(02)00335-x

  日期：2002.7

  A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.